CH403466A - Process for the production of ink- and high-moisture-strength paper - Google Patents
Process for the production of ink- and high-moisture-strength paperInfo
- Publication number
- CH403466A CH403466A CH991161A CH991161A CH403466A CH 403466 A CH403466 A CH 403466A CH 991161 A CH991161 A CH 991161A CH 991161 A CH991161 A CH 991161A CH 403466 A CH403466 A CH 403466A
- Authority
- CH
- Switzerland
- Prior art keywords
- phenyl
- ethyl
- parts
- carbostyril
- textiles
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 2
- 239000004753 textile Substances 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 238000005282 brightening Methods 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 4
- UMNWFDSXJVFCBQ-UHFFFAOYSA-N 7-amino-3-phenyl-1h-quinolin-2-one Chemical class O=C1NC2=CC(N)=CC=C2C=C1C1=CC=CC=C1 UMNWFDSXJVFCBQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- QKLCQKPAECHXCQ-UHFFFAOYSA-N ethyl phenylglyoxylate Chemical compound CCOC(=O)C(=O)C1=CC=CC=C1 QKLCQKPAECHXCQ-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- DSBIJCMXAIKKKI-UHFFFAOYSA-N 5-nitro-o-toluidine Chemical class CC1=CC=C([N+]([O-])=O)C=C1N DSBIJCMXAIKKKI-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 239000007844 bleaching agent Substances 0.000 description 2
- LISFMEBWQUVKPJ-UHFFFAOYSA-N carbostyril Natural products C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- CYYCGNNGNFMKMN-UHFFFAOYSA-N 1-ethyl-7-(ethylamino)-3-phenylquinolin-2-one Chemical compound CCNC1=CC=C2C=C(C(=O)N(CC)C2=C1)C1=CC=CC=C1 CYYCGNNGNFMKMN-UHFFFAOYSA-N 0.000 description 1
- ONUKVSFEFHPRKD-UHFFFAOYSA-N 7-(dimethylamino)-1-ethyl-3-phenylquinolin-2-one Chemical compound O=C1N(CC)C2=CC(N(C)C)=CC=C2C=C1C1=CC=CC=C1 ONUKVSFEFHPRKD-UHFFFAOYSA-N 0.000 description 1
- SVJDUPWOWXKPER-UHFFFAOYSA-N 7-(dimethylamino)-3-(3,5-dimethylphenyl)-1-methylquinolin-2-one Chemical compound CN(C)C1=CC=C2C=C(C3=CC(C)=CC(C)=C3)C(=O)N(C)C2=C1 SVJDUPWOWXKPER-UHFFFAOYSA-N 0.000 description 1
- PSBDIRWJOBDDEI-UHFFFAOYSA-N 7-(dimethylamino)-3-phenyl-1h-quinolin-2-one Chemical compound O=C1NC2=CC(N(C)C)=CC=C2C=C1C1=CC=CC=C1 PSBDIRWJOBDDEI-UHFFFAOYSA-N 0.000 description 1
- FAMRVDRNNRCDFL-UHFFFAOYSA-N 7-amino-1-ethyl-3-phenylquinolin-2-one Chemical compound O=C1N(CC)C2=CC(N)=CC=C2C=C1C1=CC=CC=C1 FAMRVDRNNRCDFL-UHFFFAOYSA-N 0.000 description 1
- IJCLOOKYCQWSJA-UHFFFAOYSA-N 7-amino-3-phenylchromen-2-one Chemical class O=C1OC2=CC(N)=CC=C2C=C1C1=CC=CC=C1 IJCLOOKYCQWSJA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ONOSEGAWZJGEBF-UHFFFAOYSA-N CCN1C(=O)C(=CC2=CC=C(C=C12)N(C)C)C1=CC(Cl)=CC=C1 Chemical compound CCN1C(=O)C(=CC2=CC=C(C=C12)N(C)C)C1=CC(Cl)=CC=C1 ONOSEGAWZJGEBF-UHFFFAOYSA-N 0.000 description 1
- OROCXQUJPTWDNF-UHFFFAOYSA-N CN(C)C1=CC=C2C=C(C3=CC=C(C)C=C3)C(=O)N(C)C2=C1 Chemical compound CN(C)C1=CC=C2C=C(C3=CC=C(C)C=C3)C(=O)N(C)C2=C1 OROCXQUJPTWDNF-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- -1 chlorine and bromine Chemical class 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- JGBJNRPKVSUFSM-UHFFFAOYSA-N n-ethyl-2-methyl-5-nitroaniline Chemical compound CCNC1=CC([N+]([O-])=O)=CC=C1C JGBJNRPKVSUFSM-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 235000019794 sodium silicate Nutrition 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000271 synthetic detergent Substances 0.000 description 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H23/00—Processes or apparatus for adding material to the pulp or to the paper
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/20—Macromolecular organic compounds
- D21H17/33—Synthetic macromolecular compounds
- D21H17/34—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D21H17/37—Polymers of unsaturated acids or derivatives thereof, e.g. polyacrylates
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/20—Macromolecular organic compounds
- D21H17/33—Synthetic macromolecular compounds
- D21H17/46—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D21H17/47—Condensation polymers of aldehydes or ketones
- D21H17/49—Condensation polymers of aldehydes or ketones with compounds containing hydrogen bound to nitrogen
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/20—Macromolecular organic compounds
- D21H17/33—Synthetic macromolecular compounds
- D21H17/46—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D21H17/54—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen
- D21H17/55—Polyamides; Polyaminoamides; Polyester-amides
Description
Verwendung von 3- Phenyl-7-amino-carbostyril-V erbindungen als optische
Aufhellungsmittel für Textilien
Die vorliegende Erfindung bezieht sich auf die Verwendung von 3-Phenyl-7-amino-carbostyril-Verbindungen der Formel
EMI1.1
worin RI, Ro, R und R1 unabhängig voneinander für Wasserstoff oder für niedere Alkylgruppen, wie Methyloder Athylgruppen stehen, während R5, Rs und R7 unabhängig voneinander Wasserstoff-, Alkylgruppen, wie Methyl- und Athylgruppen, Alkoxygruppen, wie Methoxy- und Athoxygruppen, oder Halogen, wie Chlor und Brom, bedeuten, als optische Aufhellungsmittel für Textilien.
Es wurde bereits vorgeschlagen, als optische Aufhellungsmittel für Textilien 3-Phenyl-7-amino-cumarine zu verwenden. Bei Anwendung dieser Verbindungen werden jedoch stark gelbgrünstichige Aufhellungseffekte erzielt. Demgegenüber werden mit den erfindungsgemäss verwendeten Aufhellungsmitteln reinweisse, in bekannter Weise leicht bläulich fluoreszierende, Aufhellungswirkungen erhalten.
Die erfindungsgemäss verwendeten Aufhellungsmittel eignen sich zum Aufhellen der verschiedenartigsten textilen Materialien, vor allem zum Aufhellen von Fasern, Fäden, Geweben oder Gewirken synthetischer Herkunft, insbesondere zum Aufhellen von Textilmaterialien aus Polyvinylchlorid und Polyamiden.
2
Die Aufhellungsmittel können in üblicher Weise angewandt werden, z. B. in Form von wässrigen Dispersionen oder in Form von Lösungen in indifferenten organischen Lösungsmitteln; gewünschtenfalls kann man die Aufhellungsmittel auch in Kombination mit Waschmitteln anwenden. Die jeweils erforderlichen Mengen an Aufhellungsmitteln lassen sich durch Vorversuche leicht ermitteln; im allgemeinen genügen Mengen von 0,1-1 S an Aufhellungsmittel, bezogen auf das Gewicht des zu behandelnden Materials.
Die erfindungsgemäss als Aufhellungsmittel zu verwendenden Verbindungen sind beispielsweise dadurch erhältlich, dass man 2-Amino-4-nitro-toluole der Formel
EMI1.2
mit Phenylglyoxylsäureäthylestern der Formel
EMI1.3
zu 3-Phenyl-7-nitro-carbostyrilen der Formel
EMI2.1
kondcnsiert, die Nitrogruppe zur Aminogruppe reduziert und diese gegebenenfalls alkyliert. In den Formeln haben R1 und R4 bis R7 die eingangs angegebene Bedeutung.
Die in den folgenden Beispielen angegebenen Teile sind Gewichtsteile.
Beispiel I
Textilien aus Celluloseacetat oder synthetischen Polyamiden, die gelblich aussehen, werden in üblicher Weise mit einem Waschmittel gewaschen, welches ausser etwa 20 " synthetischen waschaktiven Substanzen und komplexen Phosphaten, Natriumsilikat, Carboxymethylcellulose sowie Natriumperborat noch 0,2 l-Athyl-3- phenyl-7-dimethylamino-carbostyril enthält. Die Texti lien besitzen dann ein strahlend weisses Aussehen.
Das verwendete Aufhellungsmittel war in folgender Weise hergestellt worden:
17,9 Teile 2-Äthylamino-4-nitrotoluol, 16,2 Teile Phenylglyoxylsäureäthylester und 2 Teile Piperidin wurden unter Rühren 8 Stunden auf 2000 C erhitzt. 1 8 Teile des so erhaltenen l-Athyl-3-phenyl-7-nitro-carbostyrils wurden dann in einer Mischung aus 50 Teilen Alkohol und 50 Teilen konz. Salzsäure auf dem Wasserbad erhitzt und unter Rühren mit einer Lösung von 50 Teilen Zinn-ll-chlorid in 100 Teilen konz. Salzsäure versetzt. Das Reaktionsgemisch wurde noch eine Stunde gerührt und hiernach abgekühlt. Das ausgefallene 1 Äthyl-3-phenyl-7 -amino-carbostyril wurde abfiltriert, mit 200 Teilen 5 % iger Natronlauge aufgekocht, dann heiss abfiltriert, getrocknet und aus Xylol umkristallisiert.
13,2 Teile des so erhaltenen l-Athyl-3-phenyl-7-amino- carbostyrils vom Schmelzpunkt 17e1720C wurden in 150 Teilen Dioxan gelöst, mit 25 Teilen etwa 35 % iger methanolischer Formaldehydlösung sowie 10 Teilen Raney-Nickel-Katalysator versetzt und dann in einem Autoklaven 4 Stunden bei einem Wasserstoffdruck von 110 atm. auf l lO' C erhitzt. Anschliessend wurde der Raney-Nickel-Katalysator abgetrennt, und das Dioxan wurde im Vakuum abdestilliert. Das hinterbleibende 1 Äthyl-3-phenyl-7-dimcthyhlmino-carbostyril besass nach dem Umkristallisieren aus Cyclohexan einen Schmelzpunkt von 109-1120 C.
Beispiel 2
Textilien aus Wolle werden in üblicher Weise mit einem für die Feinwäsche geeigneten Waschmittel, das (),l % 1 -Athyl-3-phenyl-7-dimethylamino-carbostyril ent- hält, gewaschen. Die behandelten Textilien zeigen danach ein rein weisses Aussehen.
Beispiel 3
Textilien aus Celluloseacetat, Wolle oder synthetischen Polyamiden, die ein gelblichweisses Aussehen besitzen, werden 30 Minuten bei 5 > 60'' C mit einer wässrigen Lösung behandelt, die im Liter 3 g Natriumdithionit, 1,5 g Tetranatriumpyrophosphat und 0,05 g 1 -Xthyl-3-phenyl-7-dimethylamino - carbostyril enthielt.
Die so behandelten Textilien sind dann reinweiss.
Textilien aus Polyacrylnitrilfasern können in gleicher Weise aufgehellt werden, wenn man die Behandlung mit der angeführten Lösung bei 80-100'' C durchführt.
Anstellc des in den Beispielen angeführten Aufhellungsmittels l-Athyl-3-phenyl-7-dimethylamino - carbo styril kann man auch
3-Phenyl-7-dimethylamino-carbostyril vom
Schmelzpunkt 258-262 C,
I-Methyl-3-phenyl-7-amino-carbostyril vom
Schmelzpunkt 190-192 C, I-Methyl-3-phenyl-7-dimethylamino-carbostyril vom
Schmelzpunkt 17e1730 C, 1 -Methyl-3-(4'-methylphenyl)-7-dimethylamino- carbostyril vom Schmelzpunkt 185-190" C, 1 -Methyl-3-(4'-methylphenyl)-6-methyl-7-dimethyl- amino-carbostyril vom Schmelzpunkt 152 bis
153' C,
1 -Methyl-3-(3',5'-dimethylphenyl)-7-dimethylamino carbostyril vom Schmelzpunkt 151-153 C,
1 -Athyl-3-(3'-chlorphenyl)
-7-dimethylamino- carbostyril vom Schmelzpunkt 161-162'' C, 1 -Athyl-3-phenyl-7-monoäthylamino-carbostyril vom Schmelzpunkt 178-180'' C oder 1 -Äthyl-3-phenyl-7-N-methyl-N-äthylamino-carbo styril vom Schmelzpunkt 75-78 C verwenden.
Diese Verbindungen sind in der Weise erhältlich, dass man analog zu der im Beispiel 1 angegebenen Herstellungsweise die jeweils in Betracht kommenden 2-Amino4-nitro-toluole und Phenylglyoxylsäureäthylester miteinander kondensiert, die cntstandenen Nitro-carbostyrile zu Amino-carbostyrilen reduziert und diese dann gegebenenfalls alkyliert.
Use of 3-phenyl-7-amino-carbostyril compounds as optical
Lightening agents for textiles
The present invention relates to the use of 3-phenyl-7-aminocarbostyril compounds of the formula
EMI1.1
where RI, Ro, R and R1 independently represent hydrogen or lower alkyl groups such as methyl or ethyl groups, while R5, Rs and R7 independently of one another are hydrogen, alkyl groups such as methyl and ethyl groups, alkoxy groups such as methoxy and ethoxy groups, or Halogen, like chlorine and bromine, mean as optical brightening agents for textiles.
It has already been proposed to use 3-phenyl-7-amino-coumarins as optical brightening agents for textiles. When using these compounds, however, lightening effects with a strong yellow-green tinge are achieved. In contrast, the whitening agents used according to the invention give pure white whitening effects that are slightly bluish fluorescent in a known manner.
The lightening agents used according to the invention are suitable for lightening a wide variety of textile materials, especially for lightening fibers, threads, woven or knitted fabrics of synthetic origin, in particular for lightening textile materials made of polyvinyl chloride and polyamides.
2
The lightening agents can be applied in a conventional manner, e.g. B. in the form of aqueous dispersions or in the form of solutions in inert organic solvents; if desired, the lightening agents can also be used in combination with detergents. The amounts of whitening agents required in each case can easily be determined by preliminary tests; in general, amounts of 0.1-1 S of brightening agent, based on the weight of the material to be treated, are sufficient.
The compounds to be used as lightening agents according to the invention can be obtained, for example, by adding 2-amino-4-nitro-toluenes of the formula
EMI1.2
with ethyl phenylglyoxylate of the formula
EMI1.3
to 3-phenyl-7-nitro-carbostyrils of the formula
EMI2.1
condenses, the nitro group is reduced to the amino group and this optionally alkylated. In the formulas, R1 and R4 to R7 have the meaning given at the beginning.
The parts given in the following examples are parts by weight.
Example I.
Textiles made of cellulose acetate or synthetic polyamides, which look yellowish, are washed in the usual way with a detergent which, in addition to about 20 "synthetic detergent substances and complex phosphates, sodium silicate, carboxymethyl cellulose and sodium perborate, also contains 0.2 l-ethyl-3-phenyl-7 -dimethylamino-carbostyril The textiles then have a brilliant white appearance.
The lightening agent used was made in the following way:
17.9 parts of 2-ethylamino-4-nitrotoluene, 16.2 parts of ethyl phenylglyoxylate and 2 parts of piperidine were heated to 2000 ° C. for 8 hours with stirring. 18 parts of the l-ethyl-3-phenyl-7-nitro-carbostyrils thus obtained were then concentrated in a mixture of 50 parts of alcohol and 50 parts. Hydrochloric acid heated on a water bath and concentrated while stirring with a solution of 50 parts of tin-II chloride in 100 parts. Hydrochloric acid added. The reaction mixture was stirred for a further hour and then cooled. The precipitated 1-ethyl-3-phenyl-7-amino-carbostyril was filtered off, boiled with 200 parts of 5% sodium hydroxide solution, then filtered off while hot, dried and recrystallized from xylene.
13.2 parts of the l-ethyl-3-phenyl-7-aminocarbostyril with a melting point of 17e1720C were dissolved in 150 parts of dioxane, 25 parts of about 35% strength methanolic formaldehyde solution and 10 parts of Raney nickel catalyst were added and then in an autoclave for 4 hours at a hydrogen pressure of 110 atm. heated to lO'C. The Raney nickel catalyst was then separated off and the dioxane was distilled off in vacuo. The remaining 1-ethyl-3-phenyl-7-dimcthyhlmino-carbostyril had a melting point of 109-1120 C. after recrystallization from cyclohexane.
Example 2
Textiles made of wool are washed in the usual way with a detergent suitable for delicate washing which contains (), 1% 1-ethyl-3-phenyl-7-dimethylamino-carbostyril. The treated textiles then show a pure white appearance.
Example 3
Textiles made of cellulose acetate, wool or synthetic polyamides, which have a yellowish-white appearance, are treated for 30 minutes at 5> 60 '' C with an aqueous solution containing 3 g of sodium dithionite, 1.5 g of tetrasodium pyrophosphate and 0.05 g of 1 - Xthyl-3-phenyl-7-dimethylamino - carbostyril contained.
The textiles treated in this way are then pure white.
Textiles made of polyacrylonitrile fibers can be lightened in the same way if the treatment with the above solution is carried out at 80-100 ° C.
Instead of the brightening agent l-ethyl-3-phenyl-7-dimethylamino - carbo styril can also be used
3-phenyl-7-dimethylamino-carbostyril from
Melting point 258-262 C,
I-methyl-3-phenyl-7-aminocarbostyril from
Melting point 190-192 C, I-methyl-3-phenyl-7-dimethylamino-carbostyril vom
Melting point 17e1730 C, 1-methyl-3- (4'-methylphenyl) -7-dimethylamino-carbostyril of melting point 185-190 "C, 1-methyl-3- (4'-methylphenyl) -6-methyl-7-dimethyl - Amino-carbostyril from melting point 152 to
153 'C,
1 -Methyl-3- (3 ', 5'-dimethylphenyl) -7-dimethylamino carbostyril of melting point 151-153 C,
1-ethyl-3- (3'-chlorophenyl)
-7-dimethylamino-carbostyril with a melting point of 161-162 "C, 1-ethyl-3-phenyl-7-monoethylamino-carbostyril with a melting point of 178-180" C or 1-ethyl-3-phenyl-7-N-methyl Use -N-ethylamino-carbo styril with a melting point of 75-78 C.
These compounds can be obtained by condensing the 2-amino-4-nitro-toluenes and ethyl phenylglyoxylate with one another, reducing the resulting nitro-carbostyriles to amino-carbostyrils and then alkylating them, analogously to the method of preparation given in Example 1 .
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB30241/60A GB948749A (en) | 1960-09-01 | 1960-09-01 | Improvements in the production of paper |
| GB30242/60A GB948750A (en) | 1960-09-01 | 1960-09-01 | Improvements in the production of paper |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH403466A true CH403466A (en) | 1965-11-30 |
Family
ID=26260351
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH991161A CH403466A (en) | 1960-09-01 | 1961-08-25 | Process for the production of ink- and high-moisture-strength paper |
| CH991261A CH410615A (en) | 1960-09-01 | 1961-08-25 | Process for the production of an ink-resistant and highly wet-strength paper with high tear strength |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH991261A CH410615A (en) | 1960-09-01 | 1961-08-25 | Process for the production of an ink-resistant and highly wet-strength paper with high tear strength |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US3141813A (en) |
| BE (1) | BE607429A (en) |
| CH (2) | CH403466A (en) |
| DE (2) | DE1226409B (en) |
| FR (1) | FR1297558A (en) |
| GB (2) | GB948750A (en) |
| LU (1) | LU40559A1 (en) |
| NL (4) | NL131384C (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4387144A (en) | 1977-05-11 | 1983-06-07 | Tullis Russell & Company Limited | Battery separator material |
| US4425126A (en) | 1979-12-28 | 1984-01-10 | Johnson & Johnson Baby Products Company | Fibrous material and method of making the same using thermoplastic synthetic wood pulp fibers |
| US4392861A (en) * | 1980-10-14 | 1983-07-12 | Johnson & Johnson Baby Products Company | Two-ply fibrous facing material |
| US4654100A (en) * | 1985-03-04 | 1987-03-31 | The Dow Chemical Company | Method for preparing random-fiber thermoset composites |
| US5512618A (en) * | 1993-05-07 | 1996-04-30 | Enviro-Chem, Inc. | Suspension-enhancing adhesive additive for paper manufacturing, liquid adhesive composition using same, and method of preparing liquid adhesive composition |
| US6489040B1 (en) | 2000-02-15 | 2002-12-03 | United States Gypsium Company | Wallboard with improved roll-up resistance |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE965864C (en) * | 1937-09-11 | 1957-06-27 | Albert Ag Chem Werke | Method for gluing fibrous structures such as paper, cardboard in the fabric |
| US2559220A (en) * | 1942-07-31 | 1951-07-03 | American Cyanamid Co | Manufacture of cellulose products of improved wet strength |
| GB572959A (en) * | 1943-02-15 | 1945-10-31 | William Charlton | Treatment of paper or textile fabrics |
| US2540352A (en) * | 1945-10-27 | 1951-02-06 | Munising Paper Company | Method of making wet strength paper |
| US2629699A (en) * | 1949-10-20 | 1953-02-24 | Stein Hall & Co Inc | Modified starch-urea-formaldehyde water resistant adhesive |
| US3016325A (en) * | 1955-11-01 | 1962-01-09 | Electro Chem Fiber Seal Corp | Process of combining water-insoluble additament with organic fibrous material |
| US3000777A (en) * | 1956-08-23 | 1961-09-19 | Portals Ltd | Methods of making webs of fibrous materials |
| DE1070491B (en) * | 1956-08-23 | 1959-12-03 | Portals Ltd., Whitchurch, Hampshire (Grossbritannien) | Process for the production of webs from fibrous material |
| NL238071A (en) * | 1958-04-14 | |||
| GB873700A (en) * | 1958-07-24 | 1961-07-26 | Portals Ltd | Improvements in or relating to methods for making webs of fibrous material |
-
1960
- 1960-09-01 GB GB30242/60A patent/GB948750A/en not_active Expired
- 1960-09-01 GB GB30241/60A patent/GB948749A/en not_active Expired
-
1961
- 1961-08-16 FR FR870823A patent/FR1297558A/en not_active Expired
- 1961-08-18 NL NL268380A patent/NL131384C/xx active
- 1961-08-18 NL NL268379D patent/NL268379A/xx unknown
- 1961-08-18 NL NL268379A patent/NL129158C/xx active
- 1961-08-18 NL NL268380D patent/NL268380A/xx unknown
- 1961-08-23 BE BE607429A patent/BE607429A/en unknown
- 1961-08-23 US US133305A patent/US3141813A/en not_active Expired - Lifetime
- 1961-08-23 US US133304A patent/US3141812A/en not_active Expired - Lifetime
- 1961-08-25 CH CH991161A patent/CH403466A/en unknown
- 1961-08-25 CH CH991261A patent/CH410615A/en unknown
- 1961-08-29 LU LU40559D patent/LU40559A1/xx unknown
- 1961-08-31 DE DES75537A patent/DE1226409B/en active Pending
- 1961-08-31 DE DES75536A patent/DE1222363B/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| BE607429A (en) | 1961-12-18 |
| DE1226409B (en) | 1966-10-06 |
| NL129158C (en) | 1970-07-15 |
| US3141812A (en) | 1964-07-21 |
| DE1222363B (en) | 1966-08-04 |
| GB948750A (en) | 1964-02-05 |
| NL268379A (en) | 1964-06-25 |
| FR1297558A (en) | 1962-06-29 |
| US3141813A (en) | 1964-07-21 |
| LU40559A1 (en) | 1961-10-30 |
| GB948749A (en) | 1964-02-05 |
| CH410615A (en) | 1966-03-31 |
| NL131384C (en) | |
| NL268380A (en) | 1964-06-25 |
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